Dimethylformamide → 6-phenoxy-1H-indole

HRID 1371963노트

반응식

HRID 1371963 반응식
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-])=O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]N(C=O)C>>[O:1]([C:8]1[CH:9]=[C:10]2[C:11]([CH:14]=[CH:18][NH:15]2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

3

반응물 2

HCID 6228DimethylformamideHCID 210715624-Phenoxy-1-methyl-2-nitrobenzene

생성물 1

HCID 210716106-phenoxy-1H-indole

실험 절차

Combine 4-phenoxy-1-methyl-2-nitro-benzene (6 g, 26.2 mmol) and DMF dimethylacetal (15.6 g, 131 mmol) in 60 mL dry DMF and heat at 170° C. for 16 hours. Cool to room temperature and concentrate to dryness. Dissolve residue in 50 mL EtOAc and hydrogenate with 2 g 5% Pd/C and hydrogen for 3 hours at atmospheric pressure. Filter through celite and concentragte to an oil. Purify by chromatography using Hex/EtoAC to obtain a tan solid: ISMS 210 (M+1) 1H NMR (CDCl3) 8.08 (bs, 1H), 7.61–7.59 (m, 1H), 7.34–7.29 (m, 2H), 7.18–7.17 (m, 1H), 7.18–7.0 (m, 4H), 6.92–6.89 (m, 1H), 6.56–6.54 (m, 1H).

후처리

  1. concentrationconcentrate to dryness
  2. filtrationFilter through celite and concentragte to an oil
  3. customPurify by chromatography
  4. customto obtain a tan solid

출처 및 근거

ORD 기록
ord-2705b355770f45219c177426895becf6
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157488B2

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